A series of arylazo sulfones known to cleave N?S bonds upon exposure to light have been synthesized and their activities studied in the dark and upon irradiation to DNA. Interactions with calf thymus DNA were studied and the observed significant affinities (most likely due to DNA intercalation) were analyzed by in silico molecular docking calculations, suggesting that polar contacts were predominantly through sulfonyl moieties. Incubation with plasmid pBluescript KS II showed DNA cleavage, which was examined over time and concentration. Exposure to UV-A greatly ameliorated DNA damage for most compounds, but the effect was slightly reduced under visible light. As for in vitro experiments, we found that cell death of most compounds was slightly enhanced by irradiation. Photodestructive effect under UV-A irradiation (IC50-13 ?M), (IC50-100 ?M). These compounds were irradiated in the presence of two non-cancer cell lines and found to be equally toxic only under irradiation but not in the dark. Temporal and spatial control of light may therefore provide opportunities for these new scaffolds to be useful in the development of phototoxic pharmaceuticals.
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